The solution ended up being much simpler. Whenever I have a speaker plugged into the ports on the back of the computer into the mother board, and a headset plugged into the front of the computer, everything works fine.
When there is no speaker plugged in, all of the computer audio plays through...
My gaming headset has an issue where it plays all of my computer audio through my microphone. Basically, any music, videos, or game audio I am hearing in my headset, other people can hear through my mic on Skype/Steam/etc.
I googled this issue, and went through 5 pages of people with the same...